Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Catalytic hydrolysis method of circulation phase transition for preparing benzaldehyde and benzaldehyde containing substituent

A technology of phase transfer catalysis and phase transfer catalyst, which is applied in the hydrolysis to prepare carbonyl compounds, organic chemistry, etc., can solve the problems of environmental heavy metal pollution, low reactor volume utilization rate, small reactor volume utilization rate, etc.

Active Publication Date: 2005-06-15
NANTONG TIANSHI CHEM
View PDF2 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The catalytic hydrolysis of benzylidene dichloride or substituent-containing benzylidene dichloride has been reported (GB899953, US3087967, US3524885, US4229379, US5347054), and the hydrolysis catalyst is selected from soluble zinc salts, such as zinc chloride, zinc phosphate, zinc sulfate and bromide Zinc, etc., the yield of benzaldehyde or benzaldehyde containing substituents is more than 95%, but the zinc salt catalyst is easily deactivated in excess water, affecting product quality, and seriously causing heavy metal pollution to the environment
The patent US4229379 uses concentrated hydrochloric acid as a catalyst, and the yield of benzaldehyde can reach 98%, and the HCl gas released by the reaction can be recycled after being absorbed by the packed tower, but the water consumption is relatively large, reaching 10 to 25 times the stoichiometric amount. The volume utilization rate of the device is small
[0006] In summary, the production of benzaldehyde or substituted benzaldehyde with toluene or substituted toluene as raw material by oxidation and chlorination hydrolysis has the defects of selectivity and low yield
The existing catalytic hydrolysis method using benzylidene dichloride or substituted benzylidene dichloride as raw material has problems such as heavy metal pollution of the catalyst, poor product quality, large water consumption, and low utilization rate of reactor volume.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Catalytic hydrolysis method of circulation phase transition for preparing benzaldehyde and benzaldehyde containing substituent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] In the 500ml flat-bottomed three-neck reactor with magnetic stirring, add 50g benzylidene dichloride (self-made, purity 99%), the water that weight is m1 and the benzyltriethylammonium chloride that weight is m2 respectively, control certain The reaction temperature is T1, and the reaction is stirred for t1 minutes until the reaction of the benzylidene dichloride is completed. The reaction solution was left to stand and separated to obtain an organic phase and an aqueous phase, respectively. The organic phase is weighed to obtain the weight m3, and the area percentage is determined by gas chromatography, and the mass percentage content x of benzaldehyde is calculated. See Table 1 for test results.

[0017] No.

[0018] * In Experiments 6-9, the aqueous phase of the reaction solution from Experiment 2 was used for recycling, without adding water and catalyst.

Embodiment 2

[0020] In the 500ml flat-bottomed three-neck reactor with magnetic stirring, add 50g p-chlorobenzylidene dichloride respectively (self-made, purity 99%), the water that weight is m1 and the tetraethylammonium chloride that weight is m2, control certain The reaction temperature is T1, and the reaction is stirred for t1 minute until the p-chlorobenzylidene dichloride is completely reacted. The reaction solution was kept warm and allowed to stand for stratification to obtain an organic phase and an aqueous phase respectively. The organic phase is weighed to obtain the weight m3, and the area percentage is determined by gas chromatography, and the mass percentage content x of p-chlorobenzaldehyde is calculated. See Table 2 for test results.

[0021] No.

[0022] * In Experiments 7-9, the aqueous phase of the reaction solution from Experiment 5 was used for recycling, without adding water and catalyst.

Embodiment 3

[0024] In the 500ml flat-bottomed three-neck reactor with magnetic stirring, add 50g o-chlorobenzylidene dichloride respectively (self-made, purity 99%), the water that weight is m1 and the tetrabutylammonium chloride that weight is m2, control certain The reaction temperature is T1, and the reaction is stirred for t1 minutes until the reaction of o-chlorobenzylidene dichloride is completed. The reaction solution was left to stand and separated to obtain an organic phase and an aqueous phase, respectively. The organic phase is weighed to obtain the weight m3, and the area percentage is determined by gas chromatography, and the mass percentage content x of o-chlorobenzaldehyde is calculated. See Table 3 for test results.

[0025] No.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

A process for preparing benzaldehyde or substituent benzaldehyde (C6H(5-n)XnCHO) by cyclic hydrolysis method features the hydrolyzing reaction between benzyl bichloride or substituent benzyl bichloride, water and phase-transfer catalyst at 60-110 deg.C. The water phase after reaction can be cyclically used.

Description

technical field [0001] The present invention relates to the synthesis of organic compound, more specifically adopts circulation hydrolysis method to prepare can be expressed as C 6 h (5-n) x n A new process for aromatic aldehydes of CHO (n=0, 1, 2. X can be a hydrogen atom, a halogen atom, a trifluoromethyl group, etc.). It belongs to the field of chemical manufacturing. Background technique [0002] Benzaldehyde and benzaldehyde containing substituents are important organic intermediates widely used in medicine, pesticides, spices, etc. The synthesis methods of benzaldehyde or benzaldehyde containing substituents mainly include oxidation method and chlorination hydrolysis method using toluene or toluene containing substituents as raw materials, and catalytic hydrolysis of benzylidene dichloride or benzylidene dichloride containing substituents. [0003] Oxidation methods mainly include gas-phase oxidation, liquid-phase oxidation and electrochemical oxidation. Gas-phase ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/43C07C47/54
Inventor 乔旭汤吉海崔咪芬张进平
Owner NANTONG TIANSHI CHEM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com